Holiday rentals with a patio in North Side

One of the nicest, cleanest apartments we have ever rented. Very spacious and modern. We loved the back patio and the decor throughout. Close to pretty much everything! Would definitely rent this one again!

Such a stylish and cozy spot in the heart of Andersonville! The beds were incredibly comfortable and the space had so much charm. Just steps away from great shops, restaurants, and everything else you would need near Clark street. Would definitely stay again!

Martha’s place was a real gem. It was a great apartment that was well decorated and ft very comfortable. The location felt very safe and there were great restaurants around!

Kimberly house was beyond clean and spotless. Exactly what I love when booking a Airbnb. She was very responsive and instructions were very clear. The neighborhood was quiet and peaceful. The crib look exactly like her pictures and super clean! I def would stay here again.

Great space. Actually even bigger in person than what the images are showing. Superb location. Very close to restaurants and public transport as so easy. Also walking distance to the Chicago Music Exchange, if you’re a guitar player it’s the place to visit. Sam was also extremely responsive.

At first I couldn’t believe so many 5 star reviews—and now I know why. Because you can’t give a 6. We were between business trips and have a child who lives Chicago so we thought we’d make a weekend of it rather than flying home. Lovely, homey, classy, unique, comfortable, warm and very cool all in one place. You need only to roll out of the door to find great food, great people and great fun. Thank you for opening your home to us.

Such a beautiful, cozy space! Very comfortable beds, the perfect coffee setup and fast WiFi gave us the ability to work and play. Plus our host was incredibly responsive and communicative. Would definitely stay again!

Great 1st floor town home on the boarder between Rogers Park and Evanston, right on the waters of Lake Michigan. Lots of sunlight (and able to watch the sunrise over Lake Michigan in the morning) and a couple of parks next door. The bathrooms (especially the showers) were great--full size, nice water pressure. I was able to work remotely while I was there without any issues. As others have noted, parking is on the street; but if you're proactive or book with Spot Hero or similar, it's very manageable. I really enjoyed my stay!

I traveled to Chicago for work and had a nice three-day stay here. The Airbnb is in a great location, clean, and well-equipped with thoughtful amenities. I particularly enjoyed the small library!

We were 4 adult and 1 dog and we stayed at Matthew's place, everything went smooth and easy to feel at home, parking spot and great location of the house make us everything easier, it was so fast to get to the downtonw in lees than 20 minutes. Matthew was always responsive to all our questions, I definitely will search for this place to sray on my next trip to chicago.

Such a great place to stay

Adam was a great host and very responsive. We loved our stay. The house was clean and the house is easily accessible to everything. Would definitely recommend!

This was my second stay at this location, and our family had the BEST time! We stayed for five days. The house is very immaculate; not a trace of dirt or dust anywhere. Like last time, we were left with some yummy snacks and treats upon arrival. Kris & Daniel also went above and beyond when we wanted to go to the beach - they personally came right over and got some beach chairs, towels, and an umbrella from the basement for us. The house is very comfortable with high-tech smart devices and we were nice and cool despite the heat (and nice and warm when it got chilly later in our visit). Our last day, I accidentally pulled down a curtain rod when opening the drapes, and Kris & Daniel could not have been more gracious about it. Great house and great hosts! Thank you!

This is our second stay at this location and we hope to return again in the future. It is a very well-maintained place in a safe location. Also, we love how clean it is!

I enjoyed my stay. It was clean and pleasant. Marilyn was very friendly and quick to respond to any questions I had. I would recommend staying at this Airbnb! Great time!

This was our second time staying here, and everything was as comfortable as the first time. We highly recommend this place.

A Designer’s Dream – Absolute Perfection! This home is truly exceptional—every detail reflects thoughtful design and top-tier quality. It’s a designer’s dream, with stunning décor, a comfortable and beautifully clean space, and every amenity you could possibly need. The furnishings and finishes are stylish and well appointed, making the entire experience feel luxurious and relaxing. But the real showstopper? The backyard! It’s like a second living room—lush, tranquil, and designed for ultimate comfort and enjoyment. We loved spending time out there and honestly didn’t want to leave. It's so much better than anything a hotel could even begin to provide! We will absolutely be back!

We enjoyed a week of comfortable stay at Matt’s place! We were a family of 5 people and had enough space for everyone! We came for my daughter’s wedding and it was great to have lots of things/amenities that helped us prepare for the wedding! Garage spot was helpful! Backyard peaceful and we spent some time relaxing on the deck! Adorable cozy duplex with everything you need for the relaxed and comfortable stay! Matt was respectful, helpful and very responsive! Area is great as well! Thank you so much!!

The condo is in a quiet and attractive neighborhood and the hosts answered my few questions promptly. The place was very clean and although the bedrooms were small, it was nice that each of us (nana and two teens) could have their own space.

This is our 3rd time staying at Thomas and Cynthia place. We would have it no other way. Home away from home every single time.

John's place is great, just as described. Very clean and location is perfect (across the street from Pequod's). Check in/out was easy and communication was good.

One of my favorite Aibnbs of all time. The location is FUN - right in the center of the action in Northalsted. The space itself is beautiful and clean. The bedrooms are spacious, and the kitchen is well equipped. Allan was awesome and left us a bottle of prosecco to welcome us. Best part of the house is the huge covered front balcony - a front row seat to the joyous crowds, especially on the weekend. We saw a concert, walked to a Cubs game, spoiled the kids on Michigan Ave - and everyone agreed the balcony was our fave part of the trip. The rear deck is icing on the cake. We were in town so our kids could go to a concert and they also loved the area. If you're sensitive to noise, bring earplugs - all the action brings a bit of music - but really it's a steady din so super easy to tune out at bedtime. We love this place and can't wait to come back!

We had a fantastic stay at this Airbnb during our Chicago trip! The location was perfect — close to everything we wanted to see and do with our kids. The apartment was clean, well-equipped, and exactly as described. It felt like a home away from home. Check-in was smooth, and the host was responsive and helpful throughout our stay. Highly recommend for families or anyone visiting the city!

We enjoyed our time at this apartment! Nestled in the Bucktown neighborhood of the city, which is peaceful and surrounded by beautiful homes. Nearby Wicker Park and Logan Square have a lot to offer, as well as Lincoln Park (the neighborhood) not being too far away either. While the bedroom and bathroom are on the smaller side, that’s just city life and it is a perfect retreat for 1-2 people. It’s very stylish yet cozy with the decor and all updated appliances and bathroom. I would take note of the stairs for this unit in particular, as it’s on the second level but they were fine and the patio deck was nice! We really appreciated Lauren being accommodating to our late booking. We would definitely stay here again!